diff --git a/.changes/next-release/bugfix-caf370b9-c943-4ece-a4c0-81bcefa7a4f5.json b/.changes/next-release/bugfix-caf370b9-c943-4ece-a4c0-81bcefa7a4f5.json
new file mode 100644
index 00000000000..e09b9b9d4f2
--- /dev/null
+++ b/.changes/next-release/bugfix-caf370b9-c943-4ece-a4c0-81bcefa7a4f5.json
@@ -0,0 +1,4 @@
+{
+  "type" : "bugfix",
+  "description" : "Amazon Q Feature Dev: Add error messages when the upload URL expires"
+}
\ No newline at end of file
diff --git a/plugins/amazonq/chat/jetbrains-community/src/software/aws/toolkits/jetbrains/services/amazonqFeatureDev/FeatureDevExceptions.kt b/plugins/amazonq/chat/jetbrains-community/src/software/aws/toolkits/jetbrains/services/amazonqFeatureDev/FeatureDevExceptions.kt
index c23c36c5bf2..3cdbcf1c04f 100644
--- a/plugins/amazonq/chat/jetbrains-community/src/software/aws/toolkits/jetbrains/services/amazonqFeatureDev/FeatureDevExceptions.kt
+++ b/plugins/amazonq/chat/jetbrains-community/src/software/aws/toolkits/jetbrains/services/amazonqFeatureDev/FeatureDevExceptions.kt
@@ -16,6 +16,13 @@ class CodeIterationLimitError(override val message: String, override val cause:
 
 class MonthlyConversationLimitError(override val message: String, override val cause: Throwable?) : RuntimeException()
 
+class UploadURLExpired(
+    override val message: String = message(
+        "amazonqFeatureDev.exception.upload_url_expiry"
+    ),
+    override val cause: Throwable? = null,
+) : FeatureDevException(message, cause)
+
 internal fun featureDevServiceError(message: String?): Nothing =
     throw FeatureDevException(message)
 
diff --git a/plugins/amazonq/chat/jetbrains-community/src/software/aws/toolkits/jetbrains/services/amazonqFeatureDev/controller/FeatureDevController.kt b/plugins/amazonq/chat/jetbrains-community/src/software/aws/toolkits/jetbrains/services/amazonqFeatureDev/controller/FeatureDevController.kt
index 89f90bd2265..f2c37017c45 100644
--- a/plugins/amazonq/chat/jetbrains-community/src/software/aws/toolkits/jetbrains/services/amazonqFeatureDev/controller/FeatureDevController.kt
+++ b/plugins/amazonq/chat/jetbrains-community/src/software/aws/toolkits/jetbrains/services/amazonqFeatureDev/controller/FeatureDevController.kt
@@ -36,6 +36,7 @@ import software.aws.toolkits.jetbrains.services.amazonqFeatureDev.FeatureDevExce
 import software.aws.toolkits.jetbrains.services.amazonqFeatureDev.InboundAppMessagesHandler
 import software.aws.toolkits.jetbrains.services.amazonqFeatureDev.ModifySourceFolderErrorReason
 import software.aws.toolkits.jetbrains.services.amazonqFeatureDev.MonthlyConversationLimitError
+import software.aws.toolkits.jetbrains.services.amazonqFeatureDev.UploadURLExpired
 import software.aws.toolkits.jetbrains.services.amazonqFeatureDev.ZipFileError
 import software.aws.toolkits.jetbrains.services.amazonqFeatureDev.createUserFacingErrorMessage
 import software.aws.toolkits.jetbrains.services.amazonqFeatureDev.denyListedErrors
@@ -444,6 +445,12 @@ class FeatureDevController(
                 messenger.sendMonthlyLimitError(tabId = tabId)
                 messenger.sendChatInputEnabledMessage(tabId, enabled = false)
             }
+            is UploadURLExpired -> messenger.sendAnswer(
+                tabId = tabId,
+                message = err.message,
+                messageType = FeatureDevMessageType.Answer,
+                canBeVoted = true
+            )
             is FeatureDevException -> {
                 messenger.sendError(
                     tabId = tabId,
@@ -471,7 +478,6 @@ class FeatureDevController(
                     ),
                 )
             }
-
             else -> {
                 var msg = createUserFacingErrorMessage("$FEATURE_NAME request failed: ${err.message ?: err.cause?.message}")
                 val isDenyListedError = denyListedErrors.any { msg?.contains(it) ?: false }
diff --git a/plugins/amazonq/chat/jetbrains-community/src/software/aws/toolkits/jetbrains/services/amazonqFeatureDev/util/UploadArtifact.kt b/plugins/amazonq/chat/jetbrains-community/src/software/aws/toolkits/jetbrains/services/amazonqFeatureDev/util/UploadArtifact.kt
index 0d88929ee33..66177d5a21f 100644
--- a/plugins/amazonq/chat/jetbrains-community/src/software/aws/toolkits/jetbrains/services/amazonqFeatureDev/util/UploadArtifact.kt
+++ b/plugins/amazonq/chat/jetbrains-community/src/software/aws/toolkits/jetbrains/services/amazonqFeatureDev/util/UploadArtifact.kt
@@ -14,6 +14,7 @@ import software.aws.toolkits.jetbrains.services.amazonq.CONTENT_SHA256
 import software.aws.toolkits.jetbrains.services.amazonq.SERVER_SIDE_ENCRYPTION
 import software.aws.toolkits.jetbrains.services.amazonq.SERVER_SIDE_ENCRYPTION_AWS_KMS_KEY_ID
 import software.aws.toolkits.jetbrains.services.amazonqFeatureDev.FEATURE_NAME
+import software.aws.toolkits.jetbrains.services.amazonqFeatureDev.UploadURLExpired
 import software.aws.toolkits.jetbrains.services.amazonqFeatureDev.clients.FeatureDevClient
 import software.aws.toolkits.jetbrains.services.amazonqFeatureDev.uploadCodeError
 import java.io.File
@@ -36,9 +37,13 @@ fun uploadArtifactToS3(url: String, fileToUpload: File, checksumSha256: String,
                 connection.setFixedLengthStreamingMode(fileToUpload.length())
                 IoUtils.copy(fileToUpload.inputStream(), connection.outputStream)
             }
-    } catch (err: Exception) {
+    } catch (err: HttpRequests.HttpStatusException) {
         logger.warn(err) { "$FEATURE_NAME: Failed to upload code to S3" }
-        uploadCodeError()
+
+        when (err.statusCode) {
+            403 -> throw UploadURLExpired()
+            else -> uploadCodeError()
+        }
     }
 }
 
diff --git a/plugins/core/resources/resources/software/aws/toolkits/resources/MessagesBundle.properties b/plugins/core/resources/resources/software/aws/toolkits/resources/MessagesBundle.properties
index 50418a9c139..b575a7213df 100644
--- a/plugins/core/resources/resources/software/aws/toolkits/resources/MessagesBundle.properties
+++ b/plugins/core/resources/resources/software/aws/toolkits/resources/MessagesBundle.properties
@@ -72,6 +72,7 @@ amazonqFeatureDev.exception.request_failed=Request failed
 amazonqFeatureDev.exception.retry_request_failed=Retry request failed
 amazonqFeatureDev.exception.throttling=I'm sorry, I'm experiencing high demand at the moment and can't generate your code. This attempt won't count toward usage limits. Please try again.
 amazonqFeatureDev.exception.upload_code=I'm sorry, I couldn't upload your workspace artifacts to Amazon S3 to help you with this task. You might need to allow access to the S3 bucket. For more information, see the [Amazon Q documentation](https://docs.aws.amazon.com/amazonq/latest/qdeveloper-ug/security_iam_manage-access-with-policies.html#data-perimeters) or contact your network or organization administrator.
+amazonqFeatureDev.exception.upload_url_expiry=I'm sorry, I wasn't able to generate code. A connection timed out or became unavailable. Please try again or check the following:\n\n- Exclude non-essential files in your workspace's `.gitignore`.\n\n- Check that your network connection is stable.
 amazonqFeatureDev.follow_instructions_for_authentication=Follow instructions to re-authenticate ...
 amazonqFeatureDev.follow_up.close_session=No, thanks
 amazonqFeatureDev.follow_up.incorrect_source_folder=The folder you chose isn't in your open workspace folder. You can add this folder to your workspace, or choose a folder in your open workspace.